Although a large number of methods are known for the direct hydroxylation of diamondoids, none is both practical and economically feasible for large scale manufacturing. For example, the hydroxylation of adamantane can be carried out with ozone/silica gel at very low temperature (Cohen, Z. et al, Organic Synthesis 59, 176-182 (1980), Cohen, Z. et al., J. Org. Chem. 40, 2141 (1975), chromium trioxide (Landa, S. et al., Z. Chem. 7(6), 233 (1967), (Linz, T. et al., Tetra. Lett. 28(52), 6581-2 (1987)); 90-95% nitric acid (Moiseev, I.K. et al., Zh. Org. Khim 11(1), 214-15 (1975)); 65% nitric acid with Br.sub.2 or KBr or HBr (Burkhard, J. et al., Czech Patent 161,526 (1975), see Chem1cal Abstract 85:P12344Ig); Vodicka, L. et al., Collect. Czech. Chem. Commun. 43(5), 1410-12 (1978), Burkhard, J. et al., Sb. Vvs. Sk. Chem.-Technol. Praze, Technol. Paliv. D39, 57-75 (1978), see Chemical Abstract, 93:149878)); fuming sulfuric acid (U.S. Pat. No. 3,646,224 to Moore); Br.sub.2 --H.sub.2 O (Kaklan, V. F. et al., USSR SU 1,221,866 (1990)): K.sub.2 Cr.sub.2 O.sub.7 -Bu.sub.4 NI-benzene (Ashkinazi, L. A. et al., USSR SU 1,518,334 (1989), Chemical Abstract 112:P178154x)); t-BuOH-CF.sub.3 CO.sub.2 H (Kovalev, V.V. et al., USSR 727,612 (1980), Shokova, E.A. et al., Neftekhimiva 21(2), 271-3 (1981), Granovskii, Yu V. et al., Vestn. Mosk. Univ., Ser. 2:Khim 27(1), 66-9 (1986)); t-BuOH and conc. H.sub.2 SO.sub.4 in acetonitrile-hexane (Arakawa, M. et al., JP 01,283,236 (1989)); peracids (with MCPBA: Takaishi, N. et al., Synthesis (4), 293-4 (1983)); with perbenzoic acid (Fossey, J. et al., Can. J. Chem. 63(3), 678-80 (1985)); substituted perbenzoic acids (Schneider, H.J. et al., J. Org. Chem. 50(23), 4609-15 (1985)); dioxiranes (dimethyldioxirane: Murray, R.W. et al., J. Amer. Chem. Soc. 108(9), 2470-2 (1986); methyltrifluoromethyldioxirane (Mello, R. et al., J. Amer. Chem. Soc. 111(17), 6749-57 (1989)); NaOCl or NaOBr or H.sub.2 O.sub.2 with manganese porphyrin (with NaOX: DePoorter, B. et al., J Mol. Catal. 31(2), 221-4 (1985); H.sub.2 O.sub.2 De Poorter, B. et al., J. Chem. Soc. Chem. Commun. (4), 341-3 (1986)); t-BuOOH with heteropolytungstate (Faraj, M. et al., J. Chem. Soc. Chem. Commun. (19), 1487-9 (1987)); concentrated sulfuric acid in (CF.sub.3 CO).sub.2 (Kovalev, V. V. et al., Zh. Oro. Khim. 23(9), 1882-6 (1987)); F.sub.2 in water-acetonitrile (Rozen, S. et al., J. Amer. Chem. Soc. 111(21), 8325-6 (1989)); or oxone (Kumaranthasan, R. et al., Org. Prep. Proceed. Int., 23(5), 651-4 (1991)
The foregoing syntheses are hindered by one or more of the following: low selectivity, high cost, large amounts of hazardous wastes requiring disposal, large amounts of expensive solvents, dangerous reagents, and very corrosive chemicals. While it would be desirable to provide a commercially useful and less expensive alternative previous studies have not provided a method for the direct hydroxylation of adamantane (Smith, G. W. et al., J. Org. Chem. 26, 2207-12 (1961): Landa, S. et al., Sb. Vvs. Sk. Chem.-Technol. Praze, Technol. Paliv. 19, 5-17 (1969), see Chemical Abstract, 74:99507h). While the Landa article addressed oxygen addition to adamantane, the disclosed method evolved adamantanone (the mono-ketone) rather than the alcohol produced by the method of this invention. Both studies used acetic acid as solvent or co-solvent and resulted in low selectivity for 1-adamantanol.